Recent advances in nickel catalyzed Suzuki-Miyaura cross coupling reaction via C-O&amp; C-N bond activation

Baviskar, Bhushan A; Ajmire, Prashant V.; Chumbhale, Deshraj S.; Khan, Mohammad Sadat; Kuchake, Vitthal G.; Singupuram, Madhavi; Laddha, Purushottam R.

doi:10.1016/j.scp.2022.100953

Cited by 11 publications

(7 citation statements)

References 98 publications

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“…The Suzuki–Miyaura, Heck, and Sonogashira reactions have become the most significant techniques for constructing CC bonds 17 . In recent years, different transition metals like Pd, 5,6,10 Ni, 18 Fe, 19 Co, 20 Zn, 21 and Ru have been widely used to synthesize various biaryls 22 . Today, catalysts based on the precious metal Pd are the most active and robust way to make carbon–carbon bonds via Suzuki coupling reactions 9–11 …”

Section: Introductionmentioning

confidence: 99%

The recent development of β‐cyclodextrin‐based catalysts system in Suzuki coupling reactions

Payamifar,

Abdouss,

Poursattar Marjani

2024

Applied Organom Chemis

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β‐Cyclodextrin has drawn significant attention as a special class of cyclic oligomers over the past few decades. They have been employed in many organic conversions as green alternative catalysts to perform satisfactorily in catalytic activity and modify the efficiency of organic reactions. Its availability, nontoxicity, low cost, renewability, and high performance in organic transformations are several benefits of cyclodextrins that have captured the interest of many research groups worldwide. In recent decades, great progress has been made in developing metal‐catalyzed coupling reactions to create carbon–carbon bonds. For the transition‐metal‐catalyzed cross‐coupling, using modified β‐cyclodextrin derivatives as catalysts is much more pleasant due to the obvious advantages such as valuable catalytic properties and the capability to create an inclusion complex with different metals. The particular purpose of this review is to summarize the application of β‐cyclodextrin‐based catalyst systems in Suzuki coupling reaction for the synthesis of biaryl compounds covering the years 2019–2023.

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Section: Introductionmentioning

confidence: 99%

The recent development of β‐cyclodextrin‐based catalysts system in Suzuki coupling reactions

Payamifar,

Abdouss,

Poursattar Marjani

2024

Applied Organom Chemis

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“…4 And while there are many exciting scientific advances emerging from development of new methodologies employing base metals, this buy in by the community that cost, natural abundance, and occasionally the pollution originating from mining and refining, rather than just the pure science associated with each metal is so pervasive that it has led to a long and (seemingly) impressive list of "supporting evidence", further advancing these concepts. Thus, in addition to the many individual papers continuously promoting this notion, 1 there are now thematic issues noting collaborations highlighting earth-abundant metal usage (complete with tabular surveys comparing costs). 5 These "short cuts" taken over the years have led to conclusions that may well be misguided, as documented herein, surrounding use of earthabundant metals.…”

Section: Introductionmentioning

confidence: 99%

The impact of earth-abundant metals as a replacement for Pd in cross coupling reactions

Lipshutz,

Gallou,

Luescher

2024

Preprint

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Substitution of one metal catalyst for another is not straightforward as simply justifying this change based on the availability and/or cost of the metals. A life cycle-like assessment was performed leading to the conclusion that the commonly held view that use of earth-abundant metals (and in this case study, Ni) are replacements for palladium most notably in cross coupling reactions, and Suzuki-Miyaura couplings, in particular, is an incomplete analysis of the entire picture. This notion can be misleading, and unfortunately derives nowadays mainly from the standpoint of cost, and to some degree, the relative natural abundance and mining impact of each metal. However, a more realistic appreciation emerges when several additional reaction parameters involved in the couplings are considered. Such an analysis unequivocally points to the major impact on climate change brought about by use of organic solvents, while the metals actually play subordinate roles in terms of CO2-release into the environment. Clearly, this study reveals that several factors contribute in various ways to the overall carbon footprint. Hence, a far more detailed analysis is required than that typically being utilized!

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“…Coupling reactions catalysed by 3d transition metal complexes have become an active research field owing to their simple raw materials and wide application. [23][24][25][26] In particular, some good Cu complex catalysts have been reported to replace toxic and/or expensive metal catalysts such as Pd or Ni complexes. 27,28 For instance, Ullmann reactions can be utilised to form C-C bonds, 29,30 C-O bonds, [31][32][33][34][35] and C-N bonds 36,37 between aryl compounds from aryl halides and arenes, phenols, and amines catalysed by copper catalysts, which have become increasingly popular owing to their high catalytic activity, low toxicity, and good cost-performance.…”

Section: Introductionmentioning

confidence: 99%

How does multi-reference computation change the catalysis chemistry? DFT and CASPT2 studies of the Cu-catalysed coupling reactions between aryl iodides and β-diketones

He,

Nakatani,

Hada

2023

Phys. Chem. Chem. Phys.

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Recent advances in nickel catalyzed Suzuki-Miyaura cross coupling reaction via C-O& C-N bond activation

Cited by 11 publications

References 98 publications

The recent development of β‐cyclodextrin‐based catalysts system in Suzuki coupling reactions

The recent development of β‐cyclodextrin‐based catalysts system in Suzuki coupling reactions

The impact of earth-abundant metals as a replacement for Pd in cross coupling reactions

How does multi-reference computation change the catalysis chemistry? DFT and CASPT2 studies of the Cu-catalysed coupling reactions between aryl iodides and β-diketones

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